


The First Time

by 101oBsEsSioNs



Category: Shameless (UK), Shameless (US)
Genre: BAMF Mandy Milkovich, BAMF Mickey Milkovich, Bottom Mickey Milkovich, Episode 1x07, First Time, First Time Bottoming, Homophobia, Ian Gallagher and Mandy Milkovich are Best Friends, Internalized Homophobia, Jealous Ian Gallagher, Jealous Mandy Milkovich, Jealous Mickey Milkovich, M/M, Mandy Milkovich Finds Out, Protective Mandy Milkovich, Top Ian Gallagher, Where do gay weiners go, episode 1x08
Language: English
Status: In-Progress
Published: 2020-10-19
Updated: 2020-10-23
Packaged: 2021-03-08 17:28:40
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,469
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27100480
Author URL: https://archiveofourown.org/users/101oBsEsSioNs/pseuds/101oBsEsSioNs
Summary: Ian didn't go over to Mickey's house for a fight but he prepared for one. And until that moment, he never expected Mickey to be anything but the toughest thug under 18 in all of chicago..Until the moment the toughest thug in Chicago was sitting on him and giving him that look and dropped his only weapon. And I'm not talking about the tire iron.
Relationships: Ian Gallagher/Mickey Milkovich
Comments: 10
Kudos: 50





	1. The First Time

**Author's Note:**

> Ive written plenty of fanfiction before as a teenager and a small bit as an older teen, 18 or so. At 19 or 20, I wrote a supernatural poem-format fanfic. But this is my first one since I got bipolar disorder that I've written. I've got a few drinks in me writing it but I've never been more proud to be writing again. Mickey and Ian's characters have given me back my desire to write and I'm ready to write until my heart gives out for them. This takes place in 1x07, their first time. I wanted to write what I know first but it definitely won't be the last you'll see. I'm a famous writer under cover as a bisexual fanboy and I'm ready to blow you away as I write more and more.

Mandy's POV

Mickey walks in and Mandy inwardly groans. He sticks his tongue out and they bitch for a second before his trail of stink follows him into his bedroom. 

Ian stands up a few moments later to use the bathroom and Mandy feels bad for him for having to face her brother of all people. If anyone is as homophobic as her father, it's Terry's golden boy, Mickey. Even Iggy wasn't as bad as Mickey's rotten ass. 

Ian's in there forever, she thinks, just as he finally exits the room..

He plops down on the couch and they talk for a minute before Mickey suddenly comes out to ruin the fun once again. Can't he see she's trying to spend time with her boyfriend? Even if he isn't really, it's nice having someone only focusing on her. And Mickey doesn't know he's not really hers. Rude motherfucker.

"Shove over, faggots." Mandy winces. Poor Ian.

She hopes Ian doesn't mind her brother being here but he's smiling so it seems allowable, unfortunately. This is way too small of a couch. If Dad wouldn't kill her, she'd get another one but he'd rather waste it at the bar.

She looks at the screen and curses Fuck, Mickey's beating her at her own game now. 

Ian's POV

"Shove over, faggots." 

Ian can't help but smile as Mickey plops down next to him and grabs the controller out of his hands. It's ironic what he says and Ian has to hold back his laugh at the utter absurdity of the situation.

Mickey trash talks a lot while simultaneously kicking Mandy's ass at the game. He doesn't know whether to be offended or impressed but he assumes that's normal when dealing with a Milkovich.

Their thighs are pressed against each other and he can't help but notice Mickey's presence. He tries to be casual but it's hard considering where Mickey's thighs were only minutes before, the back of them pressed against the front of Ian's. He can't help but think about it. He shouldn't have done it again but how could he resist? After only messing around with older guys who couldn't handle a teenager taking candy from their business without cowering in the corner, it's difficult not to fawn over Mickey's audacity. He's got balls and Ian's always been attracted to that type. Southside, bred and born, just like him. Not like Mandy's type is though. Ian is attracted the thug part itself, not fucking it out of him. He starts to drift as images take the place of his thoughts. Mickey biting a pillow to keep Ian's name off his tongue, Mickey clenching his thighs and letting out a quiet breath so as to not attract attention and that one small noise he got near the end this time..

It's hard to imagine Mickey as a fag. He never considered it before but after last time..

Damn...

Two weeks prior

"Ian prods the sleeping boy in the back, probably more gently than he should have but he's not actually looking for a fight.

Mickey picks his head up, pulling himself out of his sleepy daze, looking around. 

"Gallegher?" He asks in mild disbelief. 

"I want the gun, Mickey." Ian holds the tire iron out in front of him, ready to attack at a moment's notice. Mickey's faster though.

"Yeah alright, okay." Mickey sits up and rubs his eyes and Ian's shocked he's so willing to cooperate.

Mickey flips suddenly, grabbing Ian and throwing their bodies to the bed, wresting him down as Ian struggles to switch their positions. Mickey goes flying into the other side of the room. Guess he should be grateful for the ROTC training right about now. 

Mickey's up before Ian can even move and he's on him, back on the bed but Ian's not as prepared this time as Mickey wields the tire iron above his head, about to bash it into his skull.

This is it. This is the moment he should have been crying out and regretting he ever came here, ever even dared to believe he could beat Mickey Milkovich even sleepy eyed and with Ian toting the weapon. No one is stronger than the Milkovich boys. Terry made sure of that. 

But Mickey does move and suddenly neither does Ian. Ian holds his breath, and as quickly as hes been toppled, he's back on top and in control, even without the tire iron.

Because Mickey Milkovich's dick is hard as rock to the point Ian can see it even at this angle pushing at his sweatpants. 

The rage and determination to beat the shit out of each other melts off both boys faces at the same time and they just stare at each other. Waiting to see what the other does. 

Ian's lust must be visible from his eyes because Milkovich does the unthinkable. He bucks back and slides his ass down to Ian's hips as he whips his tank off. Ian doesnt question it, just wants to take, and take as much as he can, before Mickey realizes what's happening and it's too late. 

He sits up and Mickey rips off his shirt too and Ian pulls at the guy's sweats till their off and Ian's on top. 

In the last five seconds, he hasn't really had time to think exactly, so when his hand is slick with spit and probing Mickey's hole and he hears Mickey yelp, hes terrified. He knows he's young, probably looks like a bottom. The proper way to fuck is to ask positions first, not assume but he was so turned on by the fact that the scariest mother fucker he'd ever met in the south, besides the guy's dad, was turned on just by wresting him, he didn't have any brain cells left to consider Mickey might expect to fuck him instead. 

Lots of the guys he's screwed have tried to turn him down initially actually, just because he's a young freckle-faced teenager, but he's never felt like this before. This passion in his chest and the sheer desire coursing through his veins. 

"Oh you think just cause you're taller means you get to be on top?" Mickey snarls but it's lacking the menace Ian expected. And maybe he has a death wish but if so, so be it. Ian grins in his face, grabs his arm and flips Mickey over so quickly, he hears the breath rush out his lungs. Ian leans over Mickey, mouth next to his ear as he ruts against his bare ass, skin on skin. It's smoother than he expected but maybe his dicks just tougher than he thought. 

"Yeah,' he says, his voice soft since the biggest terror to walk the southside is still snoring away in the living room. "I do." 

And if Mickey doesn't try to move away and presses back instead, neither of them mention it. 

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

"Oh my god." 

Mickey's not loud in bed, not like Kash is or any other of Ian's conquests. Mickey's so quiet almost the entire time that Ian worries he's doing a shitty job. He's never had someone be so quiet and not even moan. He's not very loud himself and still enjoys it though, he tells himself. 

On the other hand, Ian's grateful, despite the disappointment. At least he won't wake the house. 

Just as hes gets close though and is about to pull out so he doesn't coming inside the older boy, Mickey breaks the silence. And that little quiet gasp and "oh my god" sends Ian's orgasm from a couple minutes away to right the fuck now and he comes harder than he has since his first time masterbating at 11 years old. 

He wants to make sure Mickey gets off though so he keeps going through his orgasm despite the sensitivity, pounding relentlessly into the body in front of him until Mickey let's out an honest-to-god whine and clenches so tight that Ian's seeing stars. 

"Fuck, Gallegher, fuck, fuck, fuck." Mickey bites into the pillow again at that point, groaning lowly as his body shakes slightly against Ian's. 

They lay panting, Ian still inside him for a good minute or so, until Mickey sucks in a breath and shoves him off surprisingly gently, probably more for himself considering Ian's dick still softening in his ass, but still. 

They lay there finishing catching their breath in silence.

"Huh." Ian finally speaks once he's caught his breath. He looks over at Mickey but he won't look back, head shoved to the other side of the bed. 

"That wasn't exactly what I expected when I came over."

Mickey's still silent, breathing quickly even now minutes after his release but not from the orgasm anymore. Ian might not be Lip's level of genius but he's not an idiot. 

"Hey, you good?" He asks, gently reaching over and trailing his fingers down Mickey's chest. And then his stomach. And then-

"It's been 5 minutes," Mickey snaps. "You think you can keep your hands off the good for at least another 5? I'm fast, but not that fast." 

Ian laughs but stops short as the snoring stops and they hear a crash. 

"God dammit," a voice from the other room mutters loudly. "Keep your god damn pipes away from my bottles."

Mickey's frozen and so is Ian as Terry Milkovich stroles right through the room, half naked and heads right into the bathroom without a glance towards them. He's still muttering under his breath but Ian can't hear anything but his own thoughts right now. 

If he gets caught fucking the son of the craziest mother fucker to ever cross the southside of chicago, he's gonna have his ass handed to him on a plate and then probably get shot or beaten to death. 

Terry staggers out of the bathroom, bleary eyed. "Ladies are making breakfast." 

And just when Ian thinks he hasn't noticed, Terry turns around, having realized the scene he's just taken in. He stares at them for what seems like eternity and then turns back around. 

"And put some clothes on! You two look like a couple of fags." 

The door closes and Ian's frozen for second as he trades a look with Mickey and breathes a sigh of relief. Their heads fall back against the pillows and just stay there for a second, not believing their luck.

Fuck," is the only thing he hears out of Mickey's still frozen form. He doesn't even move, just staring at the door as if Terry's going to come barreling back in with his own tire iron, or worse a gun, and beat the living shit out of them. After a minute, Mickey relaxes slightly and glances at Ian. 

Ian looks over and notices Mickey staring at him but Mickey looks away quickly enough that he assumes it was a trick of his eyes. 

They slowly get up and get dressed. Ians zipping up his pants as a movement startles him and he looks down at the bed. It's Kash's gun. Holy shit

Holy shit. He turns around and Mickey's staring again and touches his face as he looks away, the meaning of it clear as day to Ian. 

Mickey's giving back his gun in exchange for a good fuck? He doesn't think and tries to lean in. 

The other immediately turns away. "Kiss me and I'll cut your fucking tongue out." 

Well then. Ian shakes his head and pulls on his shirt as Mickey leaves the room without looking back. But the flush on his neck leaves Ian with plenty of images to jerk to for days afterwards. 

Now:

"Oh your slutty feminist ass can't take a real man beating you? Guess I'll let Gallegher play then, I got shit to do anyway, later."

Mickey gets up and throws the controller back into Ian's hands. He catches it easily and Mickey's out the door. 

Mandy stares after his form with fire in her eyes. "Ugh, I hate him!" 

Ian can't exactly say the same. 

"His fucking ego is way too big, I just want to kick him sometimes." 

"He is really good at this game," Ian compliments the other boy without thinking. Mandy glares at him. 

"You're on his side?" She huffs and throws her controller down next to her. "You know, whatever, don't stand up for me then. Go be buddies with my brother instead, see if I fucking care."

She stands up and storms into the kitchen as Ian slowly gets up and follows. 

"Sorry?" He offers. Hes happy he's gay in moments like this. Girls are way too hard to handle sometimes. 

Mandy scoots around the kitchen, pulling out a pot. "I'm making mac and cheese. I need food to plot my revenge." 

Ian grins, he can't help it. Mandy might be a bitch but she's also the fiercest, funniest girl he's ever met. She's like the female version of Mickey. If he was straight, he'd swear he was falling in love. 

Ian never had a best friend before. He had close friends but they already had best friends by the time he was close enough to them to be open, so he never really got the chance. Mandy though? Mandy was a nutshell of everything he ever wanted in a best friend plus a bunch of shit he never even thought of. It had only been a month or two and he already knew he would do anything to protect the only Milkovich female in the house. Or at least to help and comfort, since Mandy seemed perfectly capable of protecting her own self. He liked that about her. 

"You see anything weird when you went in the bathroom before?" She asked, stirring noodles in the pot. He stills. 

"Not that I can remember," he says carefully. "Why?" 

She tosses her hair over her shoulder and shrugs. "I don't know, he just doesn't usually come out when I have a guy over." 

Ian grins. "Oh yeah?" 

She continues. "Yeah. And he hasn't tried to play video games with me since we were younger. I don't think he likes women very much." 

Ian laughs and agrees without thinking. "Yeah I don't think so either." 

Thankfully Mandy is oblivious of his inner dilemma and drops the conversation. 

"It's whatever. I guess he decided to show me up one more time before he goes back to hibernating in his room or getting thrown back in juvie.".

Ian shrugs. "I guess." 

And that's the end of the conversation about Mickey. Mandy goes right from that into some talk about a girl at school laughing at her for having a stain on her pants and they start arguing about the proper way to beat up a girl as a girl versus a guy's fight. 

Ian goes home that evening with a grin on his face, thanking whatever god that exists for something he never expected to say. 

Creating the Milkovich clan. So he can date one and fuck the other and maybe keep his hands just clean enough to get them out of there one day. 

Mandy specifically deserves better than she's being dealt, but he can't help but think of Mickey too. Ian knows it's not easy to be gay on the southside. Living on the southside being secretly gay while living under the thumb of terry milkovich of all people?

Ian can't get over how brave Mickey must be to stay, and how much he deserves more. And if Ian's got anything to do with it, maybe it's the white knight Fiona bred into him as a kid, but both Mandy and Mickey Milkovich will be saved. 

He's sure of it.


	2. Mickey's First Drink

**Summary for the Chapter:**

> The first step to Mickey becoming the asshole we all know and love. And how Ian makes it better without ever realizing it.

Mickey likes to let loose sometimes. Maybe more than sometimes but with Terry hanging over him, he doesn't get to as often as he'd like. Sometimes he wishes he was shit at doing drug runs and manipulating people, or at least had poor aim so that helping his father wouldn't have turned into practically a full time job like it had nowadays. Sometimes he just wants to relax. Enjoy life and all that shit. 

He likes Ian for the basic fact that he knew how to have fun, but still play rough. Really rough. Mickey was more of a feral animal than a teenager and he needed someone tough enough to handle it. It wasn't his fault that his childhood was more filled with glocks and coke than the stolen Legos and deadbeat parents that Gallegher had grown up with. The redhead never could have handled a single one of the beatings his father had given him at six, let alone sixteen. 

He was one great fuck though, he's got to hand it to the kid. Mickey's still aching so good even hours after he left. 

But that fuck's got to be a one time thing, has to be. No way he's risking everything he's built for himself over some lanky, doe-eyed 15 year old. 

His eyes close.  
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

5 years earlier

The first time he ever drank booze with his old man occured the same day as his first unofficial felony. Well, it wasn't his very first but it was the first to leave a mark, in more ways than one. Other than just rolling joints or something, he didn't do much heavy lifting. Iggy and Colin did most of the bigger stuff. 

He was pretty late to the game for a Milkovich, honestly. Eleven years old and he had never done anything more than be a go between for drug exchanges or helped divy up coke or weed, something pretty mild for the boys in his family, even mild for some other families in the neighborhood. Drugs were nothing to Terry, practically a hobby at this point. Mickey experienced a lot of Terry's real job secondhand though. 

Sometimes he'd get off the school bus to find a stranger parked outside. His dad would tell them to wait for him and that Mickey would let them in. They even had code words and everything. Mickey liked it. He wasn't taught fear, only diligence and respect. Terry's teachings of respect only applied to paying customers and business partners though, anyone else was fair game and chump meat, as his father said. 

His father often left him alone with the strangers, sometimes even for hours as he went about his errands. Mickey liked talking to the strange men who would come in. His favorite was John. His father called him something else once but the man had introduced himself as John so he always referred to him as such.

John had an accent and tanned skin that made Mickeys own look like the body of a snowman, but always seemed to talk more Americanized with Mickey, sometimes even playing a game with him on his Xbox. He felt comfortable around him.

And he may have been just a tool to convey trust with the people his father was dealing with (father with a young son always made for smoother transactions), but he made the best out of his role knowing he would be in his father's place one day.   
He knew it was illegal work, dangerous men, and he loved it. Mickey was taught to respect and even came to rever them like heroes in the stories his teachers sometimes read to the class. They were confident in their own importance. Untouchable. Mickey craved to be one of them. 

One morning, he got his wish. His father grabbed him by the collar and he dropped the comic in his hands, courtesy of John's last visit the day before. Terry hauled him out into the living room, where he was greeted by several men standing in the living room, surrounded by several boxes. American and Russian military crates, to be specific. They'd been sitting in his father's room for weeks now but when he'd accidentally peeked in the room and saw them, his father had grabbed one of the guns poking out of the nearest box and whipped him in the face with it. 

He knew not to ask about it again.

Time to come be a man, el niño." One of the men smirked at him and ruffled his hair. 

They drove for nearly three hours in a beat up old pick up, having put the boxes inside a refrigerator box under a heavy new tarp. It was mostly back roads and Mickey was going to get nausous from the rocking back and forth over gravel and mud. Terry cursed at the inefficiency of the whole situation but they had ran out of time, it seemed. 

Mickey just wanted to get there. He was getting hungry and his father bought him fast food when they went out last time. He hoped the other men being there wouldn't fuck up his chances at another big mac. 

The truck finally pulled up to an older building. It was smaller than Mickey expected, about the size of a two car garage. He was told to wait in the car, to his disappointment. There wasn't anything good to look at and the truck was off so he couldn't listen to the radio. Boredom enveloped him. Finally after thinking about burgers and getting more and more impatient, he hopped out to stretch his short legs. Like most kids, sitting still wasn't exactly his specialty. He crouched on the ground to poke at a line of ants with his pocket knife. 

Not five minutes later, the sound of a gun going off made him freeze, and almost tumble backwards. It came from inside the building. Then another. And one more until it was finally quiet. He waited a minute before standing back up and silently creeped towards the building. He dying to know what was going on. 

He walked right into a murder scene. 

The men from the other truck, on the ground bleeding out, were surrounded by several other men he had never seen before, speaking something he wasn't familiar with. Spanish, he was pretty sure. One of the live ones glanced over as he talked casually to the others and noticed him leaning into the side of the doorway. The man grinned and beckoned him closer.

"Hey Terry! Your kid's come to join the fun!" 

Mickey was about to run, knowing the consequences of not doing what he was told but his father grinned nastily at him and nodded for him to get his ass over there as the others hooted and hollered. 

Terry tossed him the gun, safety off. He was surprised he didn't blow a hole in his own foot catching it. 

His father pointed to one of the facedown men on the floor, trying to crawl towards them as his face squeaked against the cement. "Hes making a fucking mess. Go wipe off the prints on the gun and get the bleach and hoses."

Mickey nodded and carefully stepped around the bodies. It wasn't the first time he'd seen bloodshed. He knew the drill. As he walked by though, the practically dead man from before suddenly sat up and pulled a knife, slashing at Mickey. 

He didn't think, only listened to his father yell "shoot him!" and took the shot. The man fell back, dead.

They congratulated him on the way out as he pretended not to shake, and for a reward, his father made him down ten shots in a row once they were home to "complete his transition into manhood." For the first time, he understood what people meant when they said, "I need a drink." 

His brothers were impressed, knocking him on the back and punching him, but emptiness overwhelmed his senses. He excused himself to go to bathroom but no one really noticed. As he passed Mandy's room on the way back, he heard the door squeak open and his little sister's head popped out.

"Hey Mickey.."

He raised an eyebrow. "What do you want?" 

She peeked at him through the crack in the door. 

"How'd it feel?" Mandy, only eight at the time, had asked. 

"How did what feel?" He asked, playing stupid. It was enough pretending for his dad and brothers and the pack of wolves out in the kitchen. It was a whole other thing talking to his little sister about it. 

"You know..killin' a guy?" 

She looked fascinated. And while Mickey had been feeling the shots rolling around in his small stomach as he vomited them back up minutes before, the nausea seeing his sister's excitement now was worse. 

"Um. Hurt my hand a little. The gun, I mean. It just felt like killin' a guy I guess." Mickey pauses and then slowly pulls down the side of his shorts to reveal the gauze on his hip. Mandy gasps. 

"Dude did knife me a bit before he went down though." He smirked like his brothers did when they bragged about a new scar, but he didn't feel any better. He thought being a gangster would feel stronger than this. 

"Now go to bed, this ain't some my little pony marathon, it's for adults." He snapped at her. 

She glared but obediently closed the door again, muttering under her breath, as Mickey reluctantly rejoined the men in their celebration. He didn't really know what the occasion was but it didn't matter much anymore. When you kill people, you celebrate apparently. Grown ups were weird. 

And that night after all the men left, he finally let it out. His pillow muffled his screams and after a whole he managed to sob himself to sleep, the image of John's face, a bullet through his mouth, permantly etched into his brain. 

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

Mickey lays there, thoughts drifting as he rehashes the day's events. His head nods to the side and he involuntarily glances down to see his jeans have slipped a bit, exposing his hip and the scar he knows is waiting on it, front and center. He's desensitized by now from the whole event for the most part but still tries to avoid thinking about it. It's easier that way, he tells himself, forgetting what a pathetic sniveling loser he used to be.

But after a second, his eyes focus and widen. The scar is no longer there. 

Or at least isn't as visible as before, he realizes after a moment. Mickey stares at the dark finger-shaped bruises covering his hip, including one directly over his old scar. He should kill the kid for marking him like this but..fuck, he can't help smiling. 

He gently touches the bruise. Huh. 

If he was Mandy he would have seen it as a sign, but Milkovich men don't believe in fairy story bullshit. So he chucks it off to a pleasant coincidence and takes a well-deserved nap. Gallegher sure can fuck. 

..maybe he could go for another round sometime after all.

**Author's Note:**

> Please. Give me any tips or advice you want. I'm a well known writer, especially on wattpad, and my specialty is lgbt sci-fi but Mickey and Ian's relationship and all of Shameless in general brings out something in me I haven't let myself feel in a long time. I appreciate comments more than I've ever appreciated likes ot kudos. If you want me to write more, tell me what scenes or what scenarios youre desiring. I'm a good writer, drinking, writing, and fighting are really my only passions. Even if this isnt exactly my best work, I promise it'll improve. It's just been a long time since I've had time to write. I appreciate anyone reading.


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